EP2170796B1 - 3-(4-hydroxy-3-methoxyphenyl)-1-(4-hydroxyphenyl)-1-propanone and use thereof as an antimicrobial active ingredient - Google Patents
3-(4-hydroxy-3-methoxyphenyl)-1-(4-hydroxyphenyl)-1-propanone and use thereof as an antimicrobial active ingredient Download PDFInfo
- Publication number
- EP2170796B1 EP2170796B1 EP08775054A EP08775054A EP2170796B1 EP 2170796 B1 EP2170796 B1 EP 2170796B1 EP 08775054 A EP08775054 A EP 08775054A EP 08775054 A EP08775054 A EP 08775054A EP 2170796 B1 EP2170796 B1 EP 2170796B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- hydroxy
- methoxyphenyl
- hydroxyphenyl
- compound
- propanone
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- 239000004599 antimicrobial Substances 0.000 title claims description 7
- BPRALSKZBQABSR-UHFFFAOYSA-N 3-(4-hydroxy-3-methoxyphenyl)-1-(4-hydroxyphenyl)propan-1-one Chemical compound C1=C(O)C(OC)=CC(CCC(=O)C=2C=CC(O)=CC=2)=C1 BPRALSKZBQABSR-UHFFFAOYSA-N 0.000 title description 19
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- FHKSXSQHXQEMOK-UHFFFAOYSA-N hexane-1,2-diol Chemical compound CCCCC(O)CO FHKSXSQHXQEMOK-UHFFFAOYSA-N 0.000 description 1
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- 229950004531 hexyldecanoic acid Drugs 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
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- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 230000002427 irreversible effect Effects 0.000 description 1
- 229940113096 isoceteth 20 Drugs 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 229910052622 kaolinite Inorganic materials 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229960004194 lidocaine Drugs 0.000 description 1
- UWKAYLJWKGQEPM-UHFFFAOYSA-N linalool acetate Natural products CC(C)=CCCC(C)(C=C)OC(C)=O UWKAYLJWKGQEPM-UHFFFAOYSA-N 0.000 description 1
- 239000003589 local anesthetic agent Substances 0.000 description 1
- 229960005015 local anesthetics Drugs 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 229910001629 magnesium chloride Inorganic materials 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 229960004011 methenamine Drugs 0.000 description 1
- 229940095102 methyl benzoate Drugs 0.000 description 1
- 239000004530 micro-emulsion Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- NALMPLUMOWIVJC-UHFFFAOYSA-N n,n,4-trimethylbenzeneamine oxide Chemical compound CC1=CC=C([N+](C)(C)[O-])C=C1 NALMPLUMOWIVJC-UHFFFAOYSA-N 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 230000017066 negative regulation of growth Effects 0.000 description 1
- 230000007433 nerve pathway Effects 0.000 description 1
- 229910000273 nontronite Inorganic materials 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 230000009965 odorless effect Effects 0.000 description 1
- LLEMOWNGBBNAJR-UHFFFAOYSA-N ortho-phenyl-phenol Natural products OC1=CC=CC=C1C1=CC=CC=C1 LLEMOWNGBBNAJR-UHFFFAOYSA-N 0.000 description 1
- 235000010292 orthophenyl phenol Nutrition 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- 230000001717 pathogenic effect Effects 0.000 description 1
- WCVRQHFDJLLWFE-UHFFFAOYSA-N pentane-1,2-diol Chemical compound CCCC(O)CO WCVRQHFDJLLWFE-UHFFFAOYSA-N 0.000 description 1
- 210000000578 peripheral nerve Anatomy 0.000 description 1
- 239000008177 pharmaceutical agent Substances 0.000 description 1
- 229960005323 phenoxyethanol Drugs 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 229940096825 phenylmercury Drugs 0.000 description 1
- DCNLOVYDMCVNRZ-UHFFFAOYSA-N phenylmercury(.) Chemical compound [Hg]C1=CC=CC=C1 DCNLOVYDMCVNRZ-UHFFFAOYSA-N 0.000 description 1
- PETXWIMJICIQTQ-UHFFFAOYSA-N phenylmethoxymethanol Chemical compound OCOCC1=CC=CC=C1 PETXWIMJICIQTQ-UHFFFAOYSA-N 0.000 description 1
- 229910052615 phyllosilicate Inorganic materials 0.000 description 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000223 polyglycerol Chemical class 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 229940078491 ppg-15 stearyl ether Drugs 0.000 description 1
- 229960001807 prilocaine Drugs 0.000 description 1
- MVFGUOIZUNYYSO-UHFFFAOYSA-N prilocaine Chemical compound CCCNC(C)C(=O)NC1=CC=CC=C1C MVFGUOIZUNYYSO-UHFFFAOYSA-N 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- MCSINKKTEDDPNK-UHFFFAOYSA-N propyl propionate Chemical compound CCCOC(=O)CC MCSINKKTEDDPNK-UHFFFAOYSA-N 0.000 description 1
- FGVVTMRZYROCTH-UHFFFAOYSA-N pyridine-2-thiol N-oxide Chemical compound [O-][N+]1=CC=CC=C1S FGVVTMRZYROCTH-UHFFFAOYSA-N 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- WBHHMMIMDMUBKC-XLNAKTSKSA-N ricinelaidic acid Chemical class CCCCCC[C@@H](O)C\C=C\CCCCCCCC(O)=O WBHHMMIMDMUBKC-XLNAKTSKSA-N 0.000 description 1
- 229960003656 ricinoleic acid Drugs 0.000 description 1
- FEUQNCSVHBHROZ-UHFFFAOYSA-N ricinoleic acid Natural products CCCCCCC(O[Si](C)(C)C)CC=CCCCCCCCC(=O)OC FEUQNCSVHBHROZ-UHFFFAOYSA-N 0.000 description 1
- 229960001860 salicylate Drugs 0.000 description 1
- 229910000275 saponite Inorganic materials 0.000 description 1
- 230000037307 sensitive skin Effects 0.000 description 1
- 244000005714 skin microbiome Species 0.000 description 1
- 229910021647 smectite Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000011697 sodium iodate Substances 0.000 description 1
- 235000015281 sodium iodate Nutrition 0.000 description 1
- 229940032753 sodium iodate Drugs 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- KWVISVAMQJWJSZ-VKROHFNGSA-N solasodine Chemical compound O([C@@H]1[C@@H]([C@]2(CC[C@@H]3[C@@]4(C)CC[C@H](O)CC4=CC[C@H]3[C@@H]2C1)C)[C@@H]1C)[C@]11CC[C@@H](C)CN1 KWVISVAMQJWJSZ-VKROHFNGSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 229940098760 steareth-2 Drugs 0.000 description 1
- 229940100458 steareth-21 Drugs 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical class [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000002889 sympathetic effect Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 229920001864 tannin Polymers 0.000 description 1
- 239000001648 tannin Substances 0.000 description 1
- 235000018553 tannin Nutrition 0.000 description 1
- 229940116411 terpineol Drugs 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- UHUFTBALEZWWIH-UHFFFAOYSA-N tetradecanal Chemical compound CCCCCCCCCCCCCC=O UHUFTBALEZWWIH-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 230000002110 toxicologic effect Effects 0.000 description 1
- 231100000027 toxicology Toxicity 0.000 description 1
- 239000003053 toxin Substances 0.000 description 1
- 231100000765 toxin Toxicity 0.000 description 1
- XMLSXPIVAXONDL-UHFFFAOYSA-N trans-jasmone Natural products CCC=CCC1=C(C)CCC1=O XMLSXPIVAXONDL-UHFFFAOYSA-N 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- 229960003500 triclosan Drugs 0.000 description 1
- 239000001069 triethyl citrate Substances 0.000 description 1
- VMYFZRTXGLUXMZ-UHFFFAOYSA-N triethyl citrate Natural products CCOC(=O)C(O)(C(=O)OCC)C(=O)OCC VMYFZRTXGLUXMZ-UHFFFAOYSA-N 0.000 description 1
- 235000013769 triethyl citrate Nutrition 0.000 description 1
- AISMNBXOJRHCIA-UHFFFAOYSA-N trimethylazanium;bromide Chemical compound Br.CN(C)C AISMNBXOJRHCIA-UHFFFAOYSA-N 0.000 description 1
- 238000004879 turbidimetry Methods 0.000 description 1
- KMPQYAYAQWNLME-UHFFFAOYSA-N undecanal Chemical compound CCCCCCCCCCC=O KMPQYAYAQWNLME-UHFFFAOYSA-N 0.000 description 1
- 229960002703 undecylenic acid Drugs 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 230000036642 wellbeing Effects 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- 229940043810 zinc pyrithione Drugs 0.000 description 1
- GAWWVVGZMLGEIW-GNNYBVKZSA-L zinc ricinoleate Chemical compound [Zn+2].CCCCCC[C@@H](O)C\C=C/CCCCCCCC([O-])=O.CCCCCC[C@@H](O)C\C=C/CCCCCCCC([O-])=O GAWWVVGZMLGEIW-GNNYBVKZSA-L 0.000 description 1
- 229940100530 zinc ricinoleate Drugs 0.000 description 1
- PICXIOQBANWBIZ-UHFFFAOYSA-N zinc;1-oxidopyridine-2-thione Chemical compound [Zn+2].[O-]N1C=CC=CC1=S.[O-]N1C=CC=CC1=S PICXIOQBANWBIZ-UHFFFAOYSA-N 0.000 description 1
- 150000003755 zirconium compounds Chemical class 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/35—Ketones, e.g. benzophenone
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q15/00—Anti-perspirants or body deodorants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
- A61Q17/005—Antimicrobial preparations
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/62—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by hydrogenation of carbon-to-carbon double or triple bonds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/84—Ketones containing a keto group bound to a six-membered aromatic ring containing ether groups, groups, groups, or groups
Definitions
- the present invention relates to the antimicrobially active compound 3-(4-hydroxy-3-methoxyphenyl)-1-(4-hydroxyphenyl)-1-propanone of the following formula 1, to a method for producing this compound and to the use thereof as an antimicrobial agent for treating body odor.
- the compound is outstandingly suitable as an antimicrobial active ingredient for the cosmetic, in general for the dermatological treatment of microorganisms which cause body odor.
- Table 1 lists some microorganisms which have a strong influence on human skin.
- Microorganisms Staphylococcus epidermidis Underarm odor; body odor in general Corynebacterium xerosis Underarm odor Brevibacterium epidermidis Underarm odor; foot odor Escherichia coli Wound infections Pseudomonas aeruginosa Wound infections Malassezia furfur (syn.
- treatment should be taken to mean exerting any kind influence on the microorganisms in question, in which multiplication of these microorganisms is inhibited and/or the microorganisms are killed.
- Antibacterial dihydrochalcones having different substitution pattern are disclosed in Journal of Natural Products vol. 57, no. 1 pp. 18-26, 1994 and Planta Med vol. 67 pp. 186-188, 2001 .
- an antimicrobial active ingredient which is active in particular against microorganisms such as Corynebacterium xerosis, Staphylococcus epidermidis and Brevibacterium epidermidis, which cause body odor and foot odor, and which in so doing preferably also satisfies one or more of the above-stated secondary conditions.
- the novel compound according to the invention of the formula 1, namely 3-(4-hydroxy-3-methoxyphenyl)-1-(4-hydroxyphenyl)-1-propanone has excellent antimicrobial properties and in particular is active against the stated microorganisms. Further investigations into its chemical properties revealed that the compound is distinguished by high stability, in particular by elevated temperature stability and by high stability over a wide range of pH values, as a consequence of which it is ideally suitable for use in the most varied range of cosmetic products (cosmetic formulations), medical devices and pharmaceutical products.
- the compound according to the invention of the formula 1 is a white solid which forms a colorless solution in (cosmetic and/or pharmaceutical) carriers; furthermore, no discoloration was observed after incorporation of the compound according to the invention of the formula 1 in cosmetic products, in medical devices and in pharmaceutical preparations.
- a method for producing the compound of the formula 1 and the use thereof as an antimicrobial active ingredient in cosmetic products, in medical devices and in pharmaceutical preparations are likewise described here for the first time.
- the compound of the formula 1 has a strong antimicrobial action towards odor-forming microorganisms on human skin and may thus ideally be used as a deodorant as an alternative or supplement to known antimicrobial active ingredients (such as for example farnesol) in cosmetic products, in medical devices, in pharmaceutical products and the like.
- known antimicrobial active ingredients such as for example farnesol
- the usage concentration of the compound according to the invention of the formula 1 in a cosmetic final product is here preferably in the range between 0.001 to 10 wt%, preferably in the range between 0.005 and 5 wt.% and particularly preferably in the range between 0.01 and 1.0 wt.%, in each case relative to the total mass of the cosmetic product, the medical device or the pharmaceutical agent.
- an antimicrobially active amount of the compound according to the invention of the formula 1 is applied topically onto the human or animal body, such that growth of the microorganism(s) which are possibly present is inhibited and/or they are killed.
- the substance according to the invention of the formula 1 may also be used as a constituent of fragrance compositions (odoriferous substance compositions) and, for example, impart an antimicrobial action to a perfumed finished product.
- a particularly preferred fragrance composition comprises (a) an organoleptically active amount of a fragrance, (b) an antimicrobially active amount of the compound of the formula 1 and (c) optionally one or more carriers and/or additives. Since the proportion of perfume in a cosmetic finished product is frequently of the order of approx. 1 wt.%, a perfume which contains the compound according to the invention of the formula 1 will preferably consist to an extent of approx. 5-50 wt.% of the compound of the formula 1. It has proved particularly advantageous that the compound of the formula 1 has a weak intrinsic odor pronounced of vanilla pods; this characteristic makes it ideally suitable for use as a deodorizing active ingredient in a fragrance composition.
- the invention also relates to antimicrobial compositions which, in addition to (a) an antimicrobially active amount of the compound according to the invention of the formula 1, also comprise (b) a carrier substance compatible with component (a).
- the compound according to the invention of the formula 1 may be obtained by a production method which comprises the following step:
- the compound according to the invention of the formula 1 may preferably be obtained by a production method which comprises the following steps:
- the unsaturated ketone 3-(4-hydroxy-3-methoxyphenyl)-1-(4-hydroxyphenyl)-2-propen-1-one of reaction step a) is known from the literature, for example from DE 1 099 732 (for the production of polycarbonates), DE 1 447 016 (for the production of photosensitive materials), DE 2 256 961 (for the production of epoxy resins), Chem. Pharm. Bull. 1983, 31 (1), 149-155 (investigation of the inhibition of phenylalanine ammonia-lyase), Designed Monomers and Polymers (2003), 6(2), 187-196 , High Performance Polymers (2006), 18(2), 227-240 and J.
- the cosmetic and pharmaceutical, preferably dermatological, preparations according to the invention one, two, three, four or further substances which are primarily used to inhibit growth of undesired microorganisms on or in animal organisms.
- the cosmetic and pharmaceutical, preferably dermatological, preparations according to the invention may also furthermore contain one, two, three, four or more antiperspirant active ingredients (antiperspirants) and/or odor absorbers.
- Antiperspirant active ingredients which may preferably be used are aluminum salts such as aluminum chloride, aluminum chlorohydrate, nitrate, sulfate, acetate etc..
- the use of zinc, magnesium and zirconium compounds may also be advantageous. It is primarily aluminum salts and, to a somewhat lesser extent, aluminum/zirconium salt combinations which have proved effective for use in cosmetic and pharmaceutical, preferably dermatological, antiperspirants.
- the partially neutralized and thus more skin compatible, but not quite so active aluminum hydroxychlorides are also noteworthy of mention of mention of mention of the partially neutralized and thus more skin compatible, but not quite so active aluminum hydroxychlorides.
- further substances are also feasible, such as for example a) protein-precipitating substances such as inter alia formaldehyde, glutaraldehyde, natural and synthetic tannins together with trichloroacetic acid, which bring about superficial closure of the sweat glands, b) local anesthetics (inter alia diluted solutions of for example lidocaine, prilocaine or mixtures of such substances), which switch off sympathetic supply of the sweat glands by blockading the peripheral nerve pathways, c) zeolites of the X-, A- or Y-type, which, in addition to reducing sweat secretion, also function as adsorbents for bad odors and d) botulinum toxin (toxin of the bacterium Clostridium botulinum ), which is also used in the case of hyperhydrosis, i.e. pathologically elevated sweat secretion, and whose action is based on irreversible blocking of the release of the transmitter substance acet
- Odor absorbers are for example the phyllosilicates described in DE 40 09 347 , of these in particular montmorillonite, kaolinite, nontronite, saponite, hectorite, bentonite, smectite, furthermore for example zinc salts of ricinoleic acid.
- bactericidal or bacteriostatic deodorizing substances such as for example hexachlorophene, 2,4,4'-trichloro-2'-hydroxydiphenyl ether (Irgasan), 1,6-di-(4-chlorophenyldiguanidino)hexane (chlorhexidine), 3,4,4'-trichlorocarbanilide, and the active agents described in published patent applications DE-37 40 186 , DE-39 38 140 , DE-42 04 321 , DE-42 29 707 , DE-42 29 737 , DE-42 37 081 , DE-43 09 372 , DE-43 24 219 , and contain cationically active substances, such as for example quaternary ammonium salts and odor absorbers, such as for example Grillocin ® (combination of zinc ricinoleate and various additives) or triethyl citrate, optionally in combination with ion-exchange resins.
- Cosmetic and pharmaceutical, preferably dermatological, preparations according to the invention may also in many cases advantageously contain one, two, three, four or more preservatives.
- Preservatives which are preferably selected are those such as benzoic acid and the esters and salts thereof, 4-hydroxybenzoic acid and the esters ("parabens") and salts thereof, propionic acid and the esters and salts thereof, salicylic acid, and the esters and salts thereof, 2,4-hexadienoic acid (sorbic acid) and the esters and salts thereof, formaldehyde and paraformaldehyde, 2-hydroxybiphenyl ether and the salts thereof, 2-zinc sulfidopyridine N-oxide, inorganic sulfites and bisulfites, sodium iodate, chlorobutanol, 4-ethylmercury(II) 5-amino-1,3-bis(2-hydroxybenzoic acid), the salts and esters thereof, dehydracetic acid, for
- 3-(4-hydroxy-3-methoxyphenyl)-1-(4-hydroxyphenyl)-1-propanone of the formula 1 is very particularly suitable for combating microorganisms which are responsible for body odor is based on series of investigations relating to the particularly relevant microorganisms Staphylococcus epidermidis, Corynebacterium xerosis and Brevibacterium epidermidis.
- the antimicrobial action of 3-(4-hydroxy-3-methoxyphenyl)-1-(4-hydroxyphenyl)-1-propanone is here detected with the assistance of a turbidimetric measurement method.
- Turbidity measurement is used to establish growth curves for the particular microorganism in the presence and absence of an antimicrobial active ingredient.
- a possible inhibitory action of the test substance used is identified from the profile of the growth curves. Solutions with saline or DMSO for 100% growth are prepared as a negative control.
- the active substances to be investigated are first diluted in DMSO in reaction vessels. Dilution is carried out in accordance with the concentration range to be tested and corresponds in each case to 100 times the concentration of the subsequent final concentration in the test. Testing is usually begun with a final concentration of 2000 ppm in the test. Growth curves at final concentrations of 1000 ppm, 500 ppm, 250 ppm, 125 ppm, 64 ppm, 32 ppm, 16 ppm and 8 ppm are subsequently determined.
- the bacterial cultures are then incubated in the presence of the various final concentrations of antimicrobial active ingredient for 16 h (incubation temperature: 37°C).
- the absorption values (wavelength 620 nm; measurement interval: 20 minutes) obtained over the 16 hour period of turbidimetric measurement are recorded and exported into the spreadsheet program MS Excel. Means from in each case three parallel batches are calculated and used as the basis for establishing growth curves.
- the curves of the individual test sample concentrations are compared with those for the negative controls and the MIC value (minimum inhibitory concentration) is determined.
- the MIC value is the concentration at which no further growth is observable by turbidimetry.
- Example 2.2 MIC value of 3-(4-hydroxy-3-methoxyphenyl)-1-(4-hydroxyphenyl)-1-propanone
- MIC values of the compound according to the invention, 1-propanone, 3-(4-hydroxy-3-methoxyphenyl)-1-(4-hydroxyphenyl)- were determined in accordance with the general test conditions described in 2.1.
- Complete inhibition of growth for Corynebacterium xerosis (DSM 20743) was determined at a usage concentration of just 500 ppm, so demonstrating this compound's good antimicrobial activity.
- the antimicrobially active 3-(4-hydroxy-3-methoxyphenyl)-1-(4-hydroxyphenyl)-1-propanone of the formula 1, in particular insofar as it is used against microorganisms which cause body odor, is generally applied topically in the form of solutions, creams, lotions, gels, sprays, or the like.
- administration may conveniently proceed orally (tablets, capsules, powders, drops), intravenously, intraocularly, intraperitoneally or intramuscularly or in the form of an impregnated dressing.
- the concentration of the antimicrobially active compound of the formula 1 in the (topically) administered formulations is preferably in the range from 0.001%-10 wt.%, preferably in the range from 0.005-5 wt.% and particularly preferably in the range from 0.01-1 wt.%.
- the antimicrobial active ingredient may here be used (a) preventively or (b) when required.
- the concentration of the active ingredient which is to be applied for example daily varies and depends on the physiological condition of the test subjects and on specific individual parameters such as age or body weight.
- 3-(4-Hydroxy-3-methoxyphenyl)-1-(4-hydroxyphenyl)-1-propanone may be used not only alone but also in combination with further antimicrobial active substances.
- Example F2 Roll-on (macro-emulsion)
- Example F3 Roll-on (micro-emulsion)
- Component wt.% 3-(4-Hydroxy-3-methoxyphenyl)-1-(4-hydroxyphenyl)-1-propanone of formula 1 0.25 Stearic Acid 6.50 1,2-Propylene Glycol 20.00 PEG-8 20.00 Ethylhexylglycerin 0.50 Persea Gratissima Oil 0.10 Octyldodecanol 0.10 Perfume 1.00 Water (Aqua) Ad 100 Butyloctanoic Acid 0.50 Distarch Phosphate 0.40
- Example F5 Antiperspirant cream deodorant for sensitive skin
- Component Wt.% 3-(4-Hydroxy-3-methoxyphenyl)-1-(4-hydroxyphenyl)-1-propanone of formula 1 0.20 Paraffinum Liquidum 4.50 Glyceryl Stearate 5.00 Water (Aqua) ad 100 Cetyl Alcohol 5.00 PEG-40 Stearate 2.50 Trisodium EDTA 1.50 Persea Gratissima Oil 0.10 C12-15 Alkyl Benzoate 0.50 Aluminum Chlorohydrate 30.00 C 13-16 Isoparaffin 4.50 Isohexadecane 4.50 Caprylyl Glycol (1,2-octanediol) 0.30 Perfume 0.50
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Description
-
- The compound is outstandingly suitable as an antimicrobial active ingredient for the cosmetic, in general for the dermatological treatment of microorganisms which cause body odor.
- Human skin is colonized by numerous different bacteria. Most of these bacteria are non-pathogenic and of no relevance to the physiological condition of the skin and to its odor. Others, in contrast, can have a major influence on the healthy condition of the skin. Table 1 lists some microorganisms which have a strong influence on human skin.
Table 1: Microorganisms: Staphylococcus epidermidis Underarm odor; body odor in general Corynebacterium xerosis Underarm odor Brevibacterium epidermidis Underarm odor; foot odor Escherichia coli Wound infections Pseudomonas aeruginosa Wound infections Malassezia furfur (syn. Pityrosporum ovale) Dandruff Candida albicans Candidiasis in general Trichophyton mentagrophytes Skin and nail mycoses Trichophyton rubrum Skin and nail mycoses Epidermophyton floccosum Skin and nail mycoses - Bacterial degradation of endogenous substances present in perspiration, such as for example unsaturated fatty acids, gives rise from precursors, which to a greater or lesser extent have a slight odor, to unpleasant smelling decomposition products which can have a major impact on physical well-being. Formation of the substances responsible for body odor is prevented in cosmetic applications either by using products which suppress the formation of sweat ("antiperspirants") or by using substances which inhibit the growth of human skin bacteria responsible for odor formation ("deodorants"). Species of bacteria such as Staphylococcus epidermidis, Corynebacterium xerosis and Brevibacterium epidermidis are largely responsible for the formation of underarm and foot odor, or body odor in general. There is accordingly a constant need in the cosmetics industry for new agents for treating these microorganisms and others which cause body odor (including underarm and foot odor).
- For the purposes of the present document, "treatment" should be taken to mean exerting any kind influence on the microorganisms in question, in which multiplication of these microorganisms is inhibited and/or the microorganisms are killed.
- In seeking out such antimicrobially active agents, it must be borne in mind that the substances used in cosmetic and/or pharmaceutical products must furthermore
- be toxicologically safe,
- exhibit good skin compatibility,
- be stable (in particular in conventional cosmetic and/or pharmaceutical formulations),
- preferably have a slight odor or be (largely) odorless,
- preferably be colorless and cause no discoloration, and
- be inexpensive to produce (i.e. using standard methods and/or starting from standard precursors).
- Antibacterial dihydrochalcones having different substitution pattern are disclosed in Journal of Natural Products vol. 57, no. 1 pp. 18-26, 1994 and Planta Med vol. 67 pp. 186-188, 2001.
- The search for suitable (active) substances which exhibit one or more of the stated characteristics to a sufficient extent is complicated for a person skilled in the art by the fact that there is no clear dependency between the chemical structure of a substance, on the one hand, and its biological activity towards specific microorganisms (microbes) and their stability, on the other hand. Moreover, there is no predictable connection between antimicrobial action, toxicological safety, skin compatibility and/or stability.
- It was accordingly the object of the present invention to provide an antimicrobial active ingredient which is active in particular against microorganisms such as Corynebacterium xerosis, Staphylococcus epidermidis and Brevibacterium epidermidis, which cause body odor and foot odor, and which in so doing preferably also satisfies one or more of the above-stated secondary conditions.
- It has surprisingly now been found that the novel compound according to the invention of the formula 1, namely 3-(4-hydroxy-3-methoxyphenyl)-1-(4-hydroxyphenyl)-1-propanone, has excellent antimicrobial properties and in particular is active against the stated microorganisms. Further investigations into its chemical properties revealed that the compound is distinguished by high stability, in particular by elevated temperature stability and by high stability over a wide range of pH values, as a consequence of which it is ideally suitable for use in the most varied range of cosmetic products (cosmetic formulations), medical devices and pharmaceutical products. In addition, in pure form, the compound according to the invention of the formula 1 is a white solid which forms a colorless solution in (cosmetic and/or pharmaceutical) carriers; furthermore, no discoloration was observed after incorporation of the compound according to the invention of the formula 1 in cosmetic products, in medical devices and in pharmaceutical preparations.
- A method for producing the compound of the formula 1 and the use thereof as an antimicrobial active ingredient in cosmetic products, in medical devices and in pharmaceutical preparations are likewise described here for the first time.
- The compound of the formula 1 has a strong antimicrobial action towards odor-forming microorganisms on human skin and may thus ideally be used as a deodorant as an alternative or supplement to known antimicrobial active ingredients (such as for example farnesol) in cosmetic products, in medical devices, in pharmaceutical products and the like.
- The usage concentration of the compound according to the invention of the formula 1 in a cosmetic final product is here preferably in the range between 0.001 to 10 wt%, preferably in the range between 0.005 and 5 wt.% and particularly preferably in the range between 0.01 and 1.0 wt.%, in each case relative to the total mass of the cosmetic product, the medical device or the pharmaceutical agent.
- In a preferred method for cosmetic and/or therapeutic treatment of microorganisms which cause body odor, an antimicrobially active amount of the compound according to the invention of the formula 1 is applied topically onto the human or animal body, such that growth of the microorganism(s) which are possibly present is inhibited and/or they are killed.
- The substance according to the invention of the formula 1 may also be used as a constituent of fragrance compositions (odoriferous substance compositions) and, for example, impart an antimicrobial action to a perfumed finished product. A particularly preferred fragrance composition comprises (a) an organoleptically active amount of a fragrance, (b) an antimicrobially active amount of the compound of the formula 1 and (c) optionally one or more carriers and/or additives. Since the proportion of perfume in a cosmetic finished product is frequently of the order of approx. 1 wt.%, a perfume which contains the compound according to the invention of the formula 1 will preferably consist to an extent of approx. 5-50 wt.% of the compound of the formula 1. It has proved particularly advantageous that the compound of the formula 1 has a weak intrinsic odor reminiscent of vanilla pods; this characteristic makes it ideally suitable for use as a deodorizing active ingredient in a fragrance composition.
- The invention also relates to antimicrobial compositions which, in addition to (a) an antimicrobially active amount of the compound according to the invention of the formula 1, also comprise (b) a carrier substance compatible with component (a).
- The compound according to the invention of the formula 1 may be obtained by a production method which comprises the following step:
- (b) reduction, preferably hydrogenation, of 3-(4-hydroxy-3-methoxyphenyl)-1-(4-hydroxyphenyl)-2-propen-1-one.
- The compound according to the invention of the formula 1 may preferably be obtained by a production method which comprises the following steps:
- (a) reaction (aldol condensation) of p-hydroxyacetophenone with vanillin,
- (b) reduction, preferably hydrogenation, of the reaction product obtained in step (a).
- The unsaturated ketone 3-(4-hydroxy-3-methoxyphenyl)-1-(4-hydroxyphenyl)-2-propen-1-one of reaction step a) is known from the literature, for example from
DE 1 099 732 (for the production of polycarbonates),DE 1 447 016 (for the production of photosensitive materials),DE 2 256 961 (for the production of epoxy resins), Chem. Pharm. Bull. 1983, 31 (1), 149-155 (investigation of the inhibition of phenylalanine ammonia-lyase), Designed Monomers and Polymers (2003), 6(2), 187-196, High Performance Polymers (2006), 18(2), 227-240 and J. of Macromolecular Science, Part A: Pure and Applied Chemistry (2005), A42(12), 1589-1602 (in each case for the production of polymers), Journal of Natural Products (2006), 69(2), 191-195 (detection in Allium atroviolaceum). -
- Further aspects of the present invention are disclosed by the attached claims and the following Examples. Unless otherwise stated, all stated values relate to weight.
- In various cases, it may also be advantageous to add to the cosmetic and pharmaceutical, preferably dermatological, preparations according to the invention one, two, three, four or further substances which are primarily used to inhibit growth of undesired microorganisms on or in animal organisms. Further active ingredients which may be mentioned in this respect in addition to the large group of conventional antibiotics are those products of particular relevance to cosmetics such as triclosan® (5-chloro-2-(2,4-dichlorophenoxy)phenol), climbazole, zinc pyrithione, ichthyol, Octopirox (1-hydroxy-4-methyl-6-(2,4,4-trimethylpentyl)-2(1 H)-pyridone, 2-aminoethanol), chitosan, farnesol, hexoxyglycerin, octoxyglycerin (= ethylhexylglycerin, 3-(2-ethylhexyloxy-1,2-propanediol), for example Sensiva® SC 50 from Schülke & Mayr), glycerol monolaurate, arylalkyl alcohols such as for example phenylethyl alcohol, 3-phenyl-1-propanol, veticol (4-methyl-4-phenyl-2-pentanol) or muguet alcohol (2,2-dimethyl-3-phenylpropanol), polyglycerol esters, such as for example polyglyceryl 3-caprylate, aliphatic 1,2-diols such as for example 1,2-pentanediol, 1,2-hexanediol, 1,2-octanediol, and 1,2-decanediol and alkyl-branched carboxylic acids such as 2-butyloctanoic acid, 2-butyldecanoic acid, 2-hexyloctanoic acid and 2-hexyldecanoic acid or combinations of the stated substances, which are used inter alia against underarm odor, foot odor or dandruff.
- The cosmetic and pharmaceutical, preferably dermatological, preparations according to the invention may also furthermore contain one, two, three, four or more antiperspirant active ingredients (antiperspirants) and/or odor absorbers. Antiperspirant active ingredients which may preferably be used are aluminum salts such as aluminum chloride, aluminum chlorohydrate, nitrate, sulfate, acetate etc.. In addition, however, the use of zinc, magnesium and zirconium compounds may also be advantageous. It is primarily aluminum salts and, to a somewhat lesser extent, aluminum/zirconium salt combinations which have proved effective for use in cosmetic and pharmaceutical, preferably dermatological, antiperspirants. Also worthy of mention are the partially neutralized and thus more skin compatible, but not quite so active aluminum hydroxychlorides. In addition to aluminum salts, further substances are also feasible, such as for example a) protein-precipitating substances such as inter alia formaldehyde, glutaraldehyde, natural and synthetic tannins together with trichloroacetic acid, which bring about superficial closure of the sweat glands, b) local anesthetics (inter alia diluted solutions of for example lidocaine, prilocaine or mixtures of such substances), which switch off sympathetic supply of the sweat glands by blockading the peripheral nerve pathways, c) zeolites of the X-, A- or Y-type, which, in addition to reducing sweat secretion, also function as adsorbents for bad odors and d) botulinum toxin (toxin of the bacterium Clostridium botulinum), which is also used in the case of hyperhydrosis, i.e. pathologically elevated sweat secretion, and whose action is based on irreversible blocking of the release of the transmitter substance acetylcholine which is of relevance in sweat secretion.
- Odor absorbers are for example the phyllosilicates described in
DE 40 09 347 , of these in particular montmorillonite, kaolinite, nontronite, saponite, hectorite, bentonite, smectite, furthermore for example zinc salts of ricinoleic acid. These also include bactericidal or bacteriostatic deodorizing substances, such as for example hexachlorophene, 2,4,4'-trichloro-2'-hydroxydiphenyl ether (Irgasan), 1,6-di-(4-chlorophenyldiguanidino)hexane (chlorhexidine), 3,4,4'-trichlorocarbanilide, and the active agents described in published patent applicationsDE-37 40 186 ,DE-39 38 140 ,DE-42 04 321 ,DE-42 29 707 ,DE-42 29 737 ,DE-42 37 081 ,DE-43 09 372 ,DE-43 24 219 , and contain cationically active substances, such as for example quaternary ammonium salts and odor absorbers, such as for example Grillocin® (combination of zinc ricinoleate and various additives) or triethyl citrate, optionally in combination with ion-exchange resins. - Cosmetic and pharmaceutical, preferably dermatological, preparations according to the invention may also in many cases advantageously contain one, two, three, four or more preservatives. Preservatives which are preferably selected are those such as benzoic acid and the esters and salts thereof, 4-hydroxybenzoic acid and the esters ("parabens") and salts thereof, propionic acid and the esters and salts thereof, salicylic acid, and the esters and salts thereof, 2,4-hexadienoic acid (sorbic acid) and the esters and salts thereof, formaldehyde and paraformaldehyde, 2-hydroxybiphenyl ether and the salts thereof, 2-zinc sulfidopyridine N-oxide, inorganic sulfites and bisulfites, sodium iodate, chlorobutanol, 4-ethylmercury(II) 5-amino-1,3-bis(2-hydroxybenzoic acid), the salts and esters thereof, dehydracetic acid, formic acid, 1,6-bis(4-amidino-2-bromophenoxy)-n-hexane and the salts thereof, the sodium salt of ethylmercury(II) thiosalicylic acid, phenylmercury and the salts thereof, 10-undecenoic acid and the salts thereof, 5-amino-1,3-bis(2-ethylhexyl)-5-methylhexahydropyrimidine, 5-bromo-5-nitro-1,3-dioxane, 2-bromo-2-nitro-1,3-propanediol, 2,4-dichlorobenzyl alcohol, N-(4-chlorophenyl)-N'-(3,4-dichlorophenyl)-urea, 4-chloro-m-cresol, 2,4,4'-trichloro-2'-hydroxy-diphenyl ether, 4-chloro-3,5-dimethylphenol, 1,1'-methylene-bis(3-(1-hydroxymethyl-2,4-dioximidazolidin-5-yl)urea), poly(hexamethylene biguanide) hydrochloride, 2-phenoxyethanol, hexamethylene tetramine, 1-(3-chloroallyl)-3,5,7-triaza-l-azonia adamantane chloride, 1-(4-chlorophenoxy)1(1H-imidazol-1-yl)-3,3-dimethyl-2-butanone, 1,3-bis(hydroxymethyl)-5,5-dimethyl-2,4-imidazolidindione, benzyl alcohol, Octopirox, 1,2-dibromo-2,4-dicyanobutane, 2,2'-methylene-bis(6-bromo-4-chlorophenol), bromochlorophene, mixture of 5-chloro-2-methyl-3(2H)-isothiazolinone and 2-methyl-3(2H)isothiazolinone with magnesium chloride and magnesium nitrate, 2-benzyl-4-chlorophenol, 2-chloroacetamide, chlorhexidine, chlorhexidine acetate, chlorhexidine gluconate, chlorhexidine hydrochloride, 1-phenoxy-propan-2-ol, N-alkyl(C12-C22)trimethylammonium bromide and chloride, 4,4-dimethyl-1,3-oxazolidine, N-hydroxymethyl-N-(1,3-di(hydroxymethyl)-2,5-dioxoimidazolidin-4-yl)-N'-hydroxymethylurea, 1,6-bis(4-amidino-phenoxy)-n-hexane and the salts thereof, glutaraldehyde, 5-ethyl-1-aza-3,7-dioxabicyclo(3.3.0)octane, 3-(4-chlorophenoxy)-1,2-propanediol, Hyamine, alkyl-(C8-C18)-dimethylbenzylammonium chloride, alkyl-(C8-C18)-dimethylbenzylammonium bromide, alkyl-(C8-C18)-dimethylbenzylammonium saccharinate, benzylhemiformal, 3-iodo-2-propynyl butylcarbamate, sodium hydroxymethylaminoacetate or sodium hydroxymethylaminoacetate.
- The claims and Examples below illustrate the invention or individual aspects thereof in greater detail. Unless otherwise stated, all stated values relate to weight.
- 20 g of potassium hydroxide are initially introduced into 100 g of diethylene glycol diethyl ether, heated to 120°C with stirring and combined with a mixture of 14 g of p-hydroxyacetophenone and 15 g of vanillin within 1 h. Once addition is complete, stirring is continued for a further 20 min, the mixture hydrolyzed and adjusted to pH 6-7. Once the phases have separated, the solvent is removed and 25 g of 3-(4-hydroxy-3-methoxyphenyl)-1-(4-hydroxyphenyl)-2-propen-1-one are obtained, yield: 93% of theoretical.
- 10 g of 3-(4-hydroxy-3-methoxyphenyl)-1-(4-hydroxyphenyl)-2-propen-1-one are dissolved in 100 g of tetrahydrofuran, combined with 0.2 g of Pd on activated carbon (Pd content: 5 wt.%, water content approx. 50 wt.%, in each case relative to the total mass of the catalyst) and hydrogenated at standard pressure and room temperature (approx. 20°C) After removal of the catalyst and the solvent, 9 g of 3-(4-hydroxy-3-methoxyphenyl)-1-(4-hydroxyphenyl)-propan-1-one are obtained. Yield: 89% of theoretical
- Spectroscopic data for 1-propanone, 3-(4-hydroxy-3-methoxyphenyl)-1-(4-hydroxyphenyl)- (formula 1):
- 13C-NMR (CDCl3; 75.5 MHz): δ (ppm) = 197.42(s), 161.85(s), 147.24(s), 144.44(s), 132.03(s), 130.37(d), 130.37(d), 128.18(s), 120.27(d), 115.11 (d), 115.07(d), 115.07(d), 112.53(d), 55.42(q), 39.30(t), 29.42(t);
- MS: m/z (%) = M+ ion 272(82), 151(24), 137(77), 121(100), 93(19), 65(22).
- The recognition that 3-(4-hydroxy-3-methoxyphenyl)-1-(4-hydroxyphenyl)-1-propanone of the formula 1 is very particularly suitable for combating microorganisms which are responsible for body odor is based on series of investigations relating to the particularly relevant microorganisms Staphylococcus epidermidis, Corynebacterium xerosis and Brevibacterium epidermidis.
- The antimicrobial action of 3-(4-hydroxy-3-methoxyphenyl)-1-(4-hydroxyphenyl)-1-propanone is here detected with the assistance of a turbidimetric measurement method. Turbidity measurement is used to establish growth curves for the particular microorganism in the presence and absence of an antimicrobial active ingredient. A possible inhibitory action of the test substance used is identified from the profile of the growth curves. Solutions with saline or DMSO for 100% growth are prepared as a negative control.
- The active substances to be investigated are first diluted in DMSO in reaction vessels. Dilution is carried out in accordance with the concentration range to be tested and corresponds in each case to 100 times the concentration of the subsequent final concentration in the test. Testing is usually begun with a final concentration of 2000 ppm in the test. Growth curves at final concentrations of 1000 ppm, 500 ppm, 250 ppm, 125 ppm, 64 ppm, 32 ppm, 16 ppm and 8 ppm are subsequently determined.
- The bacterial cultures are then incubated in the presence of the various final concentrations of antimicrobial active ingredient for 16 h (incubation temperature: 37°C). The absorption values (wavelength 620 nm; measurement interval: 20 minutes) obtained over the 16 hour period of turbidimetric measurement are recorded and exported into the spreadsheet program MS Excel. Means from in each case three parallel batches are calculated and used as the basis for establishing growth curves. The curves of the individual test sample concentrations are compared with those for the negative controls and the MIC value (minimum inhibitory concentration) is determined. The MIC value is the concentration at which no further growth is observable by turbidimetry.
- MIC values of the compound according to the invention, 1-propanone, 3-(4-hydroxy-3-methoxyphenyl)-1-(4-hydroxyphenyl)- were determined in accordance with the general test conditions described in 2.1. Complete inhibition of growth for Corynebacterium xerosis (DSM 20743) was determined at a usage concentration of just 500 ppm, so demonstrating this compound's good antimicrobial activity. It likewise proved possible to establish inhibition of the growth of further Gram positive bacteria which cause body odor such as Staphylococcus epidermidis (ATCC 12228), Brevibacterium epidermidis (ATCC 35514) by 3-(4-hydroxy-3-methoxyphenyl)-1-(4-hydroxyphenyl)-1-propanone in a concentration of below 0.1 wt.% using the test method described in 2.1.
- It proved possible to confirm the antimicrobial activity of 3-(4-hydroxy-3-methoxyphenyl)-1-(4-hydroxyphenyl)-1-propanone towards microorganisms which cause body odor such as Corynebacterium xerosis (DSM 20743), Staphylococcus epidermidis (ATCC 12228) and Brevibacterium epidermidis (ATCC 35514) both with the assistance of further in vitro methods such as the quantitative suspension test and by means of in vivo sniffing tests on groups of human test subjects suffering from severe body odor.
- The antimicrobially active 3-(4-hydroxy-3-methoxyphenyl)-1-(4-hydroxyphenyl)-1-propanone of the formula 1, in particular insofar as it is used against microorganisms which cause body odor, is generally applied topically in the form of solutions, creams, lotions, gels, sprays, or the like. For other purposes, administration may conveniently proceed orally (tablets, capsules, powders, drops), intravenously, intraocularly, intraperitoneally or intramuscularly or in the form of an impregnated dressing.
- The concentration of the antimicrobially active compound of the formula 1 in the (topically) administered formulations is preferably in the range from 0.001%-10 wt.%, preferably in the range from 0.005-5 wt.% and particularly preferably in the range from 0.01-1 wt.%. The antimicrobial active ingredient may here be used (a) preventively or (b) when required.
- The concentration of the active ingredient which is to be applied for example daily varies and depends on the physiological condition of the test subjects and on specific individual parameters such as age or body weight. 3-(4-Hydroxy-3-methoxyphenyl)-1-(4-hydroxyphenyl)-1-propanone may be used not only alone but also in combination with further antimicrobial active substances.
- All formulation examples F1-F5 were formulated twice using the following two perfumes separately (DPG = dipropylene glycol):
-
Fragrance material Parts by weight Acetophenone, 10% in DPG 10 n-Undecanal 5 Aldehyde C14, so-called 15 Allyl amylglycolate, 10% in DPG 20 Amyl salicylate 25 Benzyl acetate 60 Citronellol 80 d-Limonene 50 Decenol trans-9 15 Dihydromyrcenol 50 Dimethyl benzyl carbinyl acetate 30 Diphenyl oxide 5 Eucalyptol 10 Geraniol 40 Nerol 20 Geranium oil 15 Hexenol cis-3, 10% in DPG 5 Hexenyl salicylate, cis-3 20 Indole, 10% in DPG 10 Alpha-Ionone 15 Beta-Ionone 5 Lilial® (2-Methyl-3-(4-tert-butyl-phenyl)propanal) 60 Linalool 40 Methylphenyl acetate 10 Phenylethyl alcohol 225 Styrolyl acetate 20 Terpineol 30 Tetrahydrolinalool 50 Tonalide® (musk) 50 Cinnamic alcohol 10 TOTAL: 1000 -
Fragrance material Parts by weight Benzyl acetate 60 Citronellyl acetate 60 Cyclamenaldehyde (2-Methyl-3-(4-isopropylphenyl)propanal 20 Dipropylene glycol 60 Ethyllinalool 40 Florol (2-isobutyl-4-methyltetrahydro-2H-pyran-4-ol) 30 Globanone® [(E/Z)-8-cyclohexadecen-1-one] 160 Hedione® (methyl dihydrojasmonate) 130 Hexenyl salicylate, cis-3 10 Vertocitral (2,4-dimethyl-3-cyclohexencarboxaldehyde) 5 Hydratropaldehyde, 10% in DPG 5 Isodamascone (1-(2,4,4-trimethyl-2-cyclohexen-1-yl)-2-buten-1-one), 10% in DPG 5 Isomuscone (cyclohexadecanone) 85 Jacinthaflor (2-methyl-4-phenyl-1,3-dioxolane) 10 Cis-Jasmone, 10% in DPG 20 Linalool 50 Linalyl acetate 30 Methyl benzoate, 10% in DPG 25 Galaxolide® (musk) 50 Nerol 20 Phenylpropyl aldehyde 5 2-Phenylethyl alcohol 85 Tetrahydrogeraniol 15 2,2-Dimethyl-3-cyclohexyl-1-propanol 20 TOTAL: 1000 -
Component wt.% Aluminum Chlorohydrate 30.00 3-(4-Hydroxy-3-methoxyphenyl)-1-(4-hydroxyphenyl)-1-propanone of formula 1 0.10 Persea Gratissima Oil 0.10 Octyldodecanol 1.00 Dimethicone 3.00 Cyclomethicone ad 100 Perfume 7.00 Magnesium Aluminum Silicate 0.10 Disteardimonium Hectorite 4.00 Tocopheryl Acetate 0.10 Butyloctanoic acid 0.25 - 15 Parts of the mixture obtained by mixing together the listed components were filled with 85 parts by weight of a propane-butane mixture (propane:butane = 2:7 (w/w)) into an aerosol container.
-
Component wt.% 3-(4-Hydroxy-3-methoxyphenyl)-1-(4-hydroxyphenyl)-1-propanone of formula 1 0.125 Trisodium EDTA 1.50 Steareth-21 1.50 Steareth-2 2.50 PPG-15 Stearyl Ether 3.00 Aluminum Chlorohydrate 20.00 Perfume 1.00 Water (Aqua) ad 100 -
Component wt.% 3-(4-Hydroxy-3-methoxyphenyl)-1-(4-hydroxyphenyl)-1-propanone of formula 1 0.50 Aluminum Chlorohydrate 20.00 1,3-Butylene Glycol 3.00 Dicaprylyl Ether 3.00 Isoceteth-20 5.00 Glyceryl Isostearate 2.50 PEG-150 Distearate 1.00 Perfume 0.80 Water (Aqua) ad 100 -
Component wt.% 3-(4-Hydroxy-3-methoxyphenyl)-1-(4-hydroxyphenyl)-1-propanone of formula 1 0.25 Stearic Acid 6.50 1,2-Propylene Glycol 20.00 PEG-8 20.00 Ethylhexylglycerin 0.50 Persea Gratissima Oil 0.10 Octyldodecanol 0.10 Perfume 1.00 Water (Aqua) Ad 100 Butyloctanoic Acid 0.50 Distarch Phosphate 0.40 -
Component Wt.% 3-(4-Hydroxy-3-methoxyphenyl)-1-(4-hydroxyphenyl)-1-propanone of formula 1 0.20 Paraffinum Liquidum 4.50 Glyceryl Stearate 5.00 Water (Aqua) ad 100 Cetyl Alcohol 5.00 PEG-40 Stearate 2.50 Trisodium EDTA 1.50 Persea Gratissima Oil 0.10 C12-15 Alkyl Benzoate 0.50 Aluminum Chlorohydrate 30.00 C 13-16 Isoparaffin 4.50 Isohexadecane 4.50 Caprylyl Glycol (1,2-octanediol) 0.30 Perfume 0.50
Claims (7)
- The compound as claimed in claim 1 as an antimicrobial agent for treating body odor, in particular for treating underarm and foot odor.
- A method for producing the compound as claimed in claim 1, characterized by the following step:(b) reduction, preferably hydrogenation, of 3-(4-hydroxy-3-methoxyphenyl)-1-(4-hydroxyphenyl)-2-propen-1-one.
- Use of a compound as claimed in claim 1 for producing an antimicrobially active cosmetic formulation, an antimicrobially active medical device or an anti microbially active pharmaceutical formulation.
- A composition comprising the following components:(a) an antimicrobially active amount of the compound according to claim 1 and(b) a carrier substance compatible with component (a).
- The composition as claimed in claim 5, characterized in that it is a cosmetic formulation, a medical device or a pharmaceutical formulation.
- A fragrance composition comprising(a) an organoleptically active amount of a fragrance,(b) an antimicrobially active amount of the compound according to claim 1, and(c) optionally one or more carriers and/or additives.
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PCT/EP2008/059179 WO2009013166A1 (en) | 2007-07-25 | 2008-07-14 | 3-(4-hydroxy-3-methoxyphenyl)-1-(4-hydroxyphenyl)-1-propanone and use thereof as an antimicrobial active ingredient |
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US10632328B2 (en) | 2016-10-27 | 2020-04-28 | Henkel Ag & Co. Kgaa | Cosmetic agents containing a combination of at least two different active ingredients |
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---|---|---|---|---|
DE102008009929A1 (en) | 2008-02-18 | 2009-08-20 | Symrise Gmbh & Co. Kg | 3- (4-hydroxy-3-methoxyphenyl) -1 (4-hydroxyphenyl) -1-propanone and their use in cosmetic and pharmaceutical preparations |
DE102008009798B4 (en) * | 2008-02-18 | 2018-06-21 | Beiersdorf Ag | Cosmetic or dermatological preparations in the form of O / W or W / O emulsions containing 3- (4-hydroxy-3-methoxyphenyl) -1- (4-hydroxyphenyl) propan-1-one |
DE102008009749A1 (en) * | 2008-02-18 | 2009-08-20 | Beiersdorf Ag | Cosmetic or dermatological preparations containing 3- (4-hydroxy-3-methoxyphenyl) -1- (4-hydroxyphenyl) -propan-1-one and one or more cinnamic acid derivatives |
DE102008009750A1 (en) * | 2008-02-18 | 2009-08-20 | Beiersdorf Ag | Cosmetic or dermatological preparations containing 3- (4-hydroxy-3-methoxyphenyl) -1- (4-hydroxyphenyl) -propan-1-one and one or more polyols |
ES2941479T3 (en) | 2012-06-15 | 2023-05-23 | Symrise Ag | Compositions comprising agents that promote hyaluronan biosynthesis |
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DE1447016C3 (en) * | 1963-10-25 | 1973-11-15 | Kalle Ag, 6202 Wiesbaden-Biebrich | Presensitized printing plate |
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DE4229707A1 (en) | 1992-09-05 | 1994-03-10 | Beiersdorf Ag | Germicide drug combinations |
DE4237081C2 (en) | 1992-11-03 | 1996-05-09 | Beiersdorf Ag | Use of di- or triglycerol esters as Deowirkstoffe |
DE4309372C2 (en) | 1993-03-23 | 1997-08-21 | Beiersdorf Ag | Cosmetic deodorants containing mixtures of wool wax acids or wool wax acid components and fatty acid partial glycerides of unbranched fatty acids |
DE4324219C2 (en) | 1993-07-20 | 1995-08-10 | Beiersdorf Ag | Deodorant active ingredient combinations based on alpha, omega-alkane dicarboxylic acids and wool wax acids |
JP4258053B2 (en) * | 1998-03-12 | 2009-04-30 | 王子製紙株式会社 | Natural product-derived fungicides |
DE10356723A1 (en) * | 2003-12-02 | 2005-06-30 | Beiersdorf Ag | Cosmetic deodorant, selectively reducing the numbers of odor-producing skin bacteria, containing licochalcone A, optionally in the form of Glycyrrhizae inflatae root extract |
US8778987B2 (en) * | 2007-03-13 | 2014-07-15 | Symrise Ag | Use of 4-hydroxychalcone derivatives for masking an unpleasant taste |
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- 2008-07-14 US US12/670,509 patent/US8115033B2/en active Active
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Cited By (1)
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US10632328B2 (en) | 2016-10-27 | 2020-04-28 | Henkel Ag & Co. Kgaa | Cosmetic agents containing a combination of at least two different active ingredients |
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JP2010534214A (en) | 2010-11-04 |
WO2009013166A1 (en) | 2009-01-29 |
DE102007035139A1 (en) | 2009-01-29 |
US8115033B2 (en) | 2012-02-14 |
US20100254925A1 (en) | 2010-10-07 |
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